1. Cleopatra (1963) (Elizabeth Taylor and Richard Burton)
All sorts of factors can predict a movie’s spectacular financial failure: years spent in development hell, a tumultuous production process, and lavish over-spending, to name a few. But none of those portend a box-office bomb with the deadly accuracy of co-stars who hook up before, after, or during filming. Sometimes, a dud on the big screen precedes a dud on the home front: In the case of Elizabeth Taylor and Richard Burton’s troubled romance, tabloid reports of their on-again, off-again relationship were only out-scandalized by the play-by-play from the sets of the epic that nearly bankrupted 20th Century Fox. With a budget that swelled to $44 million ($236 million in today’s money), the gaudy tribute to “the siren of the Nile” was the highest grossing film of 1963—yet it only managed to recoup about half its budget during its initial run. Like the setbacks that stretched Cleopatra’s production process across three years—a change of directors, uncooperative weather, a health scare for the film’s lead—Taylor and Burton encountered multiple headline-grabbing hiccups during their two marriages; the couple separated for good in 1976.
2. Stroker Ace (1983) (Loni Anderson and Burt Reynolds)
The 1983 NASCAR comedy Stroker Ace reunited Burt Reynolds with Smokey And The Bandit and Cannonball Run director Hal Needham; unfortunately, the film did not re-team Reynolds with a romantic interest with whom he shared chemistry on and off the screen, like his Smokey squeeze Sally Field. Instead, Stroker Ace tried to synthesize fictional heat from the real-life attraction between Reynolds and future wife Loni Anderson, who played a couple with mismatched interests: driving extremely fast (him) and following Christian tenets about taking romance slowly (her). Critics couldn’t see the connection—even when Reynolds forces it with champagne and some only-acceptable-in-an-’80s-comedy harassment—and filmgoers barely saw the film at all; its paltry domestic take was the first sign of diminishing box-office fortunes that plagued Reynolds throughout the mid-’80s. It was also one of the first bumps in the couple’s time together, which ended in a messy, public divorce around the time Reynolds returned to prominence as the star of CBS’ Evening Shade.
3. Shanghai Surprise (1986) (Madonna and Sean Penn)
Arriving in theaters after a breakthrough performance in Desperately Seeking Susan and the smash success of True Blue, Shanghai Surprise proved to be one of the few disappointments of Madonna’s early career. Well, that and a rocky, whirlwind marriage to Sean Penn. A partnership that started with Penn firing a pistol at aerial photographers documenting the Ciccone-Penn nuptials, Madonna and Penn’s marriage began to unravel on the Hong Kong set of Shanghai Surprise, where it became obvious who wore the acting pants in the family. Christopher Ciccone provided the tawdry behind-the-scenes details—shouting matches, flying furniture—in his 2008 tell-all Life With My Sister Madonna, but the couple’s inability to work things out is evident in every frame of Shanghai Surprise, where one of the leading sexual icons of the 1980s understandably fails to make a convincing missionary working in 1930s China. Nonstop tabloid coverage of Madonna and Penn’s romance and an endless parade of other Indiana Jones clones didn’t exactly drive filmgoers to the local multiplex, either, and though the movie has become something of a modest camp classic, it drew only $729,885 during its opening weekend.
4. The Marrying Man (1991) (Alec Baldwin and Kim Basinger)
When news of Alec Baldwin and Kim Basinger’s separation broke in 2000, it seemed like some grand cosmic joke that the couple met making a box-office bomb where their characters are wed and divorced three times in the course of two hours. Underlining that unfortunate coincidence were moments of screwball banter like Baldwin’s “I want you every time I look at you—I just don’t want to be married to you.” Those little zingers lend the occasional lightness to a Neil Simon script steeped in noir tropes like loose-cannon mobsters and movie-studio execs with shady connections. However, when Baldwin’s charismatic heir is beaten by the second of Basinger’s criminal love interests, the sequence can’t decide whether it’s hard-boiled violence or slapstick silliness. Similarly muddled is Basinger’s performance, an attempt to move out of the femme fatale comfort zone, which earned the actress a Golden Raspberry nomination for Worst Actress. The next time the couple starred in a movie together—The Getaway, a so-so remake of the Sam Peckinpah thriller—she returned to her smoldering default setting.
5. D.O.A. (1988) (Dennis Quaid and Meg Ryan)
Dennis Quaid and Meg Ryan eventually split amid accusations of infidelity from both parties—after a highly publicized affair with Russell Crowe, Ryan stated in a 2008 interview that Quaid had been untrue “for a long time”—but for a brief period in the late ’80s, Quaid and Ryan were inseparable when it came to movie roles. The duo followed their coupling in 1987’s Innerspace with Annabel Jankel and Rocky Morton’s D.O.A., the Max Headroom creators’ stylish remake of the film-noir classic. Presaging future roles as steely heroes and cinematic flibbertigibbets to come, Quaid and Ryan create legitimate sparks as, respectively, a dying college professor and a student helping to discover who poisoned him. A man given a limited timeframe to solve his own murder is a clever-enough premise, but audiences in April of 1988 found the concept of zany cops in South Florida far more tempting—it wasn’t necessarily D.O.A. at the box office, but D.O.A. was trounced in its opening weekend by Police Academy 5: Assignment Miami Beach.
6. Bringing Out The Dead (1999) (Nicolas Cage and Patricia Arquette)
The commercial lull at the end of a strange decade for its director, Martin Scorsese’s Bringing Out The Dead provides an elegy for a place and time unmourned by many: the grimy, vice-addled New York City that was either bulldozed or covered up by urban-renewal efforts. Bringing Out The Dead takes one last, long look at the Big Apple of Taxi Driver, Mean Streets, and After Hours through the bleary eyes of Nicolas Cage’s overworked paramedic. Over the course of three taxing night shifts, the character bonds with a recovering addict played by Cage’s then-wife Patricia Arquette, and their characters’ budding relationship forms the emotional core of a film that trundles through Cage’s dark nights of the soul in a hypnotic haze. Cage and Arquette end Bringing Out The Dead in one another’s arms, but the couple filed for divorce shortly after the film’s release; Scorsese’s relationship with the box office, meanwhile, was revitalized by a depiction of an even older NYC: Gangs Of New York.
7. Cradle Will Rock (1999) (Tim Robbins and Susan Sarandon)
With a wide-ranging cast standing in for titans of American art, industry, and government, it’s a stretch to describe Cradle Will Rock as a “Tim Robbins/Susan Sarandon” vehicle. As director, producer, and screenwriter, Robbins’ role in the picture is entirely off screen; Sarandon, meanwhile, serves a supporting role opposite Rubén Blades’ Diego Rivera, playing art critic and patron (and, er, mistress to and champion of Benito Mussolini) Margherita Sarfatti. Nonetheless, the film is suffused with the spirit of the longtime couple (though never married, their partnership lasted for more than two decades), reflecting the liberal politics and ideals Robbins and Sarandon utilized to greater popular and critical acclaim in Bob Roberts and Dead Man Walking. A darling of the 1999 Cannes Film Festival, the fictionalized chronicle of the intersection between the New Deal, the labor movement, and publicly funded art in the late 1930s recouped only 8 percent of its reported $36 million budget in its limited theatrical release.
8. Swept Away (2002) (Madonna and Guy Ritchie)
Apparently there are two keys to making a successful film alongside your significant other: First, don’t remake an older movie. Second, don’t be married to Madonna. With Swept Away, her undistinguished cinematic record nearly derailed that of Snatch and Lock, Stock, And Two Smoking Barrels director Guy Ritchie, to whom she was married from 2000 to 2008. In a justly under-seen update of Lina Wertmüller’s war-of-the-sexes-and-classes comedy from 1975, Madonna plays a needling, proto-Real Housewife whose stranded-on-a-desert-isle relationship with ship’s hand Adriano Giannini goes from spite to servitude to genuine romance in an alarmingly neat-and-tidy timespan. Only when the married director and star rest on their laurels—flashy cinematography and flamboyant musical performance, respectively—does Swept Away break through the mire. Then again, 90 seconds of Madonna lip-syncing to the Della Reese recording of “Come On-A My House” is hardly enough to redeem the 87 minutes of flotsam surrounding it.
9-10. Gigli and Jersey Girl (2003, 2004) (Ben Affleck and Jennifer Lopez)
Like Madonna and Sean Penn before them—only with an overexposed music video documenting all the ways the world just wouldn’t leave them alone—public perception of Ben Affleck and Jennifer Lopez’s doomed romance had turned toxic well before they arrived on the silver screen together. Bennifer created two feature-length targets for the apathy and vitriol of the movie-going public before calling off their engagement in 2004. With a ludicrous premise—low-level gangster (Affleck) kidnaps the mentally disabled brother of a lawyer who is prosecuting his boss, while attempting to bed the uninterested lesbian (Lopez) sent to supervise him—Gigli is the Platonic ideal of a film flop: a movie so wrongheaded and sloppily assembled that the public would’ve hated it even if it weren’t already sick of Affleck and Lopez. That weariness outlasted the relationship proper, eventually causing Jersey Girl to flounder in wide release several months after the dissolution of Bennifer. Though Lopez barely appears in Kevin Smith’s attempt at mainstream warm-and-fuzzies, the damage was done. While rolling around on piles of Twilight money, Kristen Stewart and Robert Pattinson should thank their lucky sparkles that enthusiasm for supernatural romance will forever trump relationship-gossip fatigue.